Alan Jackson has his own version of the 1% vs. 99% problem, and he has to contend with it every night he's on tour.

“The problem with me is I've had 60-something singles,” said the lanky country singer and songwriter earlier this week from his home outside Nashville. Jackson, 53, was gearing up for a West Coast swing that brings him back to the Greek Theatre in Los Angeles on Friday. “It's gotten to be that there are so many songs and there's always something some of the people really want to hear and we can't always play everything. It always ends up I leave something out that somebody wanted to hear, and I feel bad.”

It's a problem that maybe 1% of working musicians face — perhaps more like one-tenth of 1% — and a problem most would give their eye teeth to have. In fact, Jackson has charted closer to 70 singles over more than two decades, about 50 of those having reached the Top 10. He could easily string together a generous concert set of two dozen songs if he only included his No. 1 hits, dating back to his first, “I'd Love You All Over Again” in 1991, through his latest, “As She's Walking Away” in 2010, on which he duetted with the Zac Brown Band.

“I do a couple,” he said. “I do [the recent single] ‘So You Don't Have to Love Me Anymore' and sometimes we do ‘Dixie Highway,'” a collaboration with Zac Brown that's on the album. “But if I replace one of the hits with something they haven't heard, sometimes that doesn't work as well. I hardly have time to mix it up much. I make my set list up every night right before the show, and it depends on where I'm playing, what I feel like, and I do like to change it up somewhat.”

“Thirty Miles West,” a reference to the distance between his hometown of Newnan, Ga., and the fabled Dixie Highway that runs through the South, is his first album since leaving the Arista Nashville Records family he'd been with since starting with the label in the late '80s. And it's the first under a new deal he's struck between his own label ACR (which stands for Alan's Country Records) and EMI.

Yet it doesn't sound drastically different from most of what he's put out throughout his career, heavy on traditional country themes and sounds, from the spry reincarnation-themed opening track “Going to Come Back as a Country Song” to the high-road approach to a breakup in “So You Don't Have to Love Me Anymore.” See the video here:

“I think I've always approached making albums pretty much the same way. I'm just looking for a mixture of songs and topics that aren't the same thing over and over,” he said. “Most are about love or heartache, so if you're not careful you can end up with 10 or 12 that sound the same. So on this one there are some personal things on there, some fun things that don't account for anything. I have songs about everything, from gospel-tinged songs, drinking songs, heartache and love songs, family songs, songs about dying, we included all that.”

The song about dying he refers to is “When I Saw You Leaving (For Nisey),” a deeply emotional exploration of how his wife Denise's cancer diagnosis in 2010 turned their world upside down. It mines a vein similar to that of “Cissy's Song,” a touching reflection on the loss of a family friend killed in a car accident several years ago. Both songs demonstrate his knack for taking on weighty, emotionally wrenching topics in a straightforward way that neither trivializes nor exploits them.

“Right after we found out about Denise's cancer, it was such a shock for us — watching her go through all this stuff, that song just came out,” he said. “I never played it for her, or told her I wrote it. I didn't know if I'd ever do anything with it. We ended up trying to record it, and it was a pretty tough one to record, but it ended up on there. I've gotten a lot of nice comments on that from people who have been through that. They said it made them feel better, or that they connected with it.”

Denise is in remission, but Jackson noted, “We had no idea till we went through it, but since we did, you see people everywhere who've gone through similar things.”

After 14 studio albums, not including his two holiday collections, Jackson says, “I don't know that there's anything too bizarre I could stretch out and do” at this point in his career.

But he's still hankering to record a straight bluegrass album — a project he started about six years ago with bluegrass queen Alison Krauss producing, but which morphed into a critically acclaimed atmospheric adult country album, “Like Red on a Rose.”

He also said he'd enjoy doing another gospel collection akin to his other 2006 album, “Precious Memories,” which he describes as something “I made for my mama,” and perhaps an entire collection of romantic ballads, “something a little more like a date-night album … not too artsy.”